The top 12 biggest Liverpool transfer disappointments

19 Mar 2002: Jari Litmanen of Liverpool celebrates after scoring the first goal with a penalty during the Liverpool v AS Roma UEFA Champions League, Group B match at Anfield, Liverpool. DIGITAL IMAGE. Mandatory Credit: Shaun Botterill/Getty Images
19 Mar 2002: Jari Litmanen of Liverpool celebrates after scoring the first goal with a penalty during the Liverpool v AS Roma UEFA Champions League, Group B match at Anfield, Liverpool. DIGITAL IMAGE. Mandatory Credit: Shaun Botterill/Getty Images
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HULL, ENGLAND – MAY 9: Alberto Aquilani of Liverpool during the Barclays Premier League match between Hull City and Liverpool at the KC Stadium on May 9, 2010 in Hull, England. (Photo by Jed Leicester/Getty Images)
HULL, ENGLAND – MAY 9: Alberto Aquilani of Liverpool during the Barclays Premier League match between Hull City and Liverpool at the KC Stadium on May 9, 2010 in Hull, England. (Photo by Jed Leicester/Getty Images)

Alberto Aquilani

Italian midfielder Alberto Aquilani was supposed to be the answer to Liverpool’s midfield problems after Xabi Alonso left, but Aquilani failed miserably and will be forever remembered as a flop.

Injuries were probably the main reason the Roma man never took off at Anfield. He somehow passed a medical despite not playing for months due to an ankle problem.

After making a brief debut in November, Aquilani finally made his full debut in December and went on to register six assist for the campaign. Not a bad return given how little he played.

But his time on Merseyside didn’t last long and the Italian returned to him homeland with AC Milan and Juventus – leaving a giant pile of ‘what ifs’ behind him.